Réaction #77503

Équation de réaction

2-iodo-benzoic acid-[3-(6-methoxy-pyridin-3-yl)-allylamide]

triethylamine

→

4-[(6-methoxy-pyridin-3-yl)-methyl]-2H-isoquinolin-1-one

Solvants

DMF

Conditions de réaction

Traitement

1. 1
   FiltrationFiltration
2. 2
   Autrethe DMF is partially evaporated on a RE
3. 3
   workup.DISSOLUTIONThe residue is dissolved with EtOAc and diluted Na2CO3 solution
4. 4
   Autrethe water phase separated
5. 5
   Extractionextraction
6. 6
   LavageThe organic phases are washed twice with water and brine
7. 7
   Séchagedried (Na2SO4)
8. 8
   Concentrationconcentrated by evaporation
9. 9
   ConcentrationColumn chromatography (SiO2, methylene chloride/acetone 3:1), concentration
10. 10
    Autreby evaporation
11. 11
    workup.STIRRINGstirring in petroleum ether

Mode opératoire

Under a N2 atmosphere, 2.04 g (5.17 mmol) of an (E/Z) mixture of 2-iodo-benzoic acid-[3-(6-methoxy-pyridin-3-yl)-allylamide], 1.53 g (5.17 mmol) of tetra-butylammonium chloride and 22 mg (0.1 mmol) of palladium diacetate are dissolved in 80 ml of DMF, then 1.8 ml (12.9 mmol) of triethylamine are added and stirring effected for 2 days at 110° C. Filtration is carried out, and the DMF is partially evaporated on a RE. The residue is dissolved with EtOAc and diluted Na2CO3 solution, the water phase separated and extraction effected twice more with EtOAc. The organic phases are washed twice with water and brine, dried (Na2SO4) and concentrated by evaporation. Column chromatography (SiO2, methylene chloride/acetone 3:1), concentration by evaporation and stirring in petroleum ether yield 4-[(6-methoxy-pyridin-3-yl)-methyl]-2H-isoquinolin-1-one; m.p. 191° C.; HPLC(gradient20-100) tRet=7.9.

Source